# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _publ_contact_author_name 'Dmitry Yufit' _publ_contact_author_address ; Department of Chemistry Durham University South Rd. Durham DH1 3LE UK ; _publ_contact_author_email d.s.yufit@durham.ac.uk _publ_contact_letter ; The CIF file contains data for the structure 1-9 from the paper Low-melting molecular complexes. Part 2. The structures of molecular complexes of tri- and di-chloromethane with small ketones and 1,4-dioxane by D.S.Yufit and J.A.K.Howard The paper will be submitted to CrystEngComm ; loop_ _publ_author_name _publ_author_address D.S.Yufit ; Department of Chemistry Durham University South Rd. Durham DH1 3LE UK ; J.A.K.Howard ; Department of Chemistry Durham University South Rd. Durham DH1 3LE UK ; #3. data data_1_CBU _database_code_depnum_ccdc_archive 'CCDC 854567' #TrackingRef '- Yufit_Howard.cif' _audit_creation_method SHELXL-97 _chemical_formula_moiety 'C4 H6 O, C H Cl3' _chemical_formula_sum 'C5 H7 Cl3 O' _chemical_formula_weight 189.46 _chemical_melting_point 200 _chemical_name_common 'chloroform cyclobutanone co-crystal' _chemical_name_systematic ; trichloromethane cyclobutanone clathrate (1:1) ; loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_angle_alpha 90.00 _cell_angle_beta 101.00(3) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 6.7004(7) _cell_length_b 8.2245(8) _cell_length_c 15.4159(15) _cell_measurement_reflns_used 1759 _cell_measurement_temperature 190.0(2) _cell_measurement_theta_max 31.03 _cell_measurement_theta_min 2.69 _cell_volume 833.91(14) _exptl_absorpt_coefficient_mu 1.021 _exptl_absorpt_correction_T_max . _exptl_absorpt_correction_T_min . _exptl_absorpt_correction_type none _exptl_absorpt_process_details . _exptl_crystal_F_000 384 _exptl_crystal_colour less _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier whitish _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.509 _exptl_crystal_density_meas . _exptl_crystal_density_method 'not measured' _exptl_crystal_description cylinder _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.3 _exptl_special_details ? _diffrn_ambient_temperature 190.0(2) _diffrn_detector 'CCD area detector' _diffrn_detector_area_resol_mean 5.6 _diffrn_detector_type 'Bruker SMART CCD 6000 area detector' _diffrn_measured_fraction_theta_full 0.833 _diffrn_measured_fraction_theta_max 0.833 _diffrn_measurement_device 'three-circle diffractometer' _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'omega scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type 'MO K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_xray_symbol K-L~3~ _diffrn_reflns_av_R_equivalents 0.0364 _diffrn_reflns_av_sigmaI/netI 0.0261 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_number 6939 _diffrn_reflns_theta_full 30.00 _diffrn_reflns_theta_max 30.00 _diffrn_reflns_theta_min 2.82 _diffrn_source 'sealed X-ray tube' _diffrn_source_current 30.0 _diffrn_source_power 1.5 _diffrn_source_target Mo _diffrn_source_voltage 50.0 _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 1685 _reflns_number_total 2027 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement 'SAINT v6.45A (Bruker, 2003)' _computing_data_collection 'Bruker SMART' _computing_data_reduction 'SAINT v6.45A (Bruker, 2003)' _computing_molecular_graphics ; OLEX2: a complete structure solution, refinement and analysis program. Dolomanov et al., J. Appl. Cryst. (2009). 42, 339-341 ; _computing_publication_material ; OLEX2: a complete structure solution, refinement and analysis program. Dolomanov et al., J. Appl. Cryst. (2009). 42, 339-341 ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)/Bruker' _refine_diff_density_max 0.361 _refine_diff_density_min -0.317 _refine_diff_density_rms 0.064 _refine_ls_R_factor_all 0.0417 _refine_ls_R_factor_gt 0.0342 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.075 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 110 _refine_ls_number_reflns 2027 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.075 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_wR_factor_gt 0.0955 _refine_ls_wR_factor_ref 0.1041 _refine_ls_weighting_details ; calc w=1/[\s^2^(Fo^2^)+(0.0700P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3 ; _refine_ls_weighting_scheme calc _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _atom_sites_solution_hydrogens difmap _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.20196(6) 0.65366(6) 0.27714(3) 0.05288(17) Uani 1 1 d . . . Cl2 Cl 0.50759(6) 0.45201(6) 0.38383(3) 0.04857(16) Uani 1 1 d . . . Cl3 Cl 0.08723(7) 0.41893(6) 0.39918(3) 0.05193(17) Uani 1 1 d . . . C1 C 0.2233(2) 0.9427(2) 0.56886(10) 0.0372(3) Uani 1 1 d . . . C1S C 0.2753(2) 0.5548(2) 0.37955(10) 0.0368(3) Uani 1 1 d . . . O1 O 0.1874(2) 0.83272(17) 0.51753(10) 0.0547(3) Uani 1 1 d . . . C3 C 0.2601(3) 1.1505(3) 0.65163(14) 0.0523(5) Uani 1 1 d . . . C4 C 0.1461(3) 0.9895(3) 0.65131(12) 0.0519(4) Uani 1 1 d . . . C2 C 0.3553(3) 1.0927(3) 0.57378(13) 0.0490(4) Uani 1 1 d . . . H1S H 0.294(3) 0.629(2) 0.4234(13) 0.038(4) Uiso 1 1 d . . . H2A H 0.335(4) 1.148(4) 0.5229(19) 0.087(9) Uiso 1 1 d . . . H2B H 0.498(5) 1.067(3) 0.5840(19) 0.088(9) Uiso 1 1 d . . . H3A H 0.174(4) 1.239(3) 0.6352(19) 0.075(8) Uiso 1 1 d . . . H3B H 0.347(4) 1.173(3) 0.7086(17) 0.072(7) Uiso 1 1 d . . . H4A H 0.004(4) 0.981(3) 0.6466(18) 0.076(7) Uiso 1 1 d . . . H4B H 0.189(5) 0.920(4) 0.700(2) 0.096(10) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0515(2) 0.0586(4) 0.0483(2) 0.01695(18) 0.00860(17) 0.00575(17) Cl2 0.0428(2) 0.0539(4) 0.0473(2) -0.00312(16) 0.00425(15) 0.00935(16) Cl3 0.0515(2) 0.0510(4) 0.0558(3) 0.00315(18) 0.01664(18) -0.00938(17) C1 0.0382(7) 0.0342(11) 0.0396(7) 0.0010(6) 0.0083(5) 0.0040(5) C1S 0.0402(7) 0.0355(10) 0.0348(6) -0.0027(6) 0.0078(5) -0.0001(6) O1 0.0548(7) 0.0434(9) 0.0677(8) -0.0178(6) 0.0165(6) -0.0020(5) C3 0.0541(9) 0.0490(14) 0.0558(10) -0.0155(8) 0.0157(8) -0.0035(8) C4 0.0631(10) 0.0533(14) 0.0441(8) -0.0004(8) 0.0226(8) -0.0065(8) C2 0.0540(9) 0.0451(13) 0.0524(9) -0.0059(8) 0.0215(8) -0.0099(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 C1S 1.7604(16) . ? Cl2 C1S 1.7615(15) . ? Cl3 C1S 1.7531(16) . ? C1 O1 1.196(2) . ? C1 C4 1.511(2) . ? C1 C2 1.511(2) . ? C1S H1S 0.90(2) . ? C3 C4 1.528(3) . ? C3 C2 1.538(3) . ? C3 H3A 0.93(3) . ? C3 H3B 0.97(3) . ? C4 H4A 0.94(3) . ? C4 H4B 0.94(3) . ? C2 H2A 0.89(3) . ? C2 H2B 0.96(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 C4 133.77(16) . . ? O1 C1 C2 133.83(15) . . ? C4 C1 C2 92.34(14) . . ? Cl3 C1S Cl1 111.25(9) . . ? Cl3 C1S Cl2 110.29(9) . . ? Cl1 C1S Cl2 110.40(8) . . ? Cl3 C1S H1S 107.8(12) . . ? Cl1 C1S H1S 109.5(13) . . ? Cl2 C1S H1S 107.5(12) . . ? C4 C3 C2 90.62(14) . . ? C4 C3 H3A 113.2(17) . . ? C2 C3 H3A 110.8(17) . . ? C4 C3 H3B 112.3(15) . . ? C2 C3 H3B 119.8(15) . . ? H3A C3 H3B 109(2) . . ? C1 C4 C3 88.43(14) . . ? C1 C4 H4A 114.8(16) . . ? C3 C4 H4A 123.9(17) . . ? C1 C4 H4B 114.5(18) . . ? C3 C4 H4B 116.4(19) . . ? H4A C4 H4B 100(2) . . ? C1 C2 C3 88.03(13) . . ? C1 C2 H2A 112.5(19) . . ? C3 C2 H2A 120.8(19) . . ? C1 C2 H2B 112.3(16) . . ? C3 C2 H2B 119.2(17) . . ? H2A C2 H2B 104(2) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C1S H1S O1 0.90(2) 2.41(2) 3.252(2) 154.9(16) . #==END data_2_dcmcbuon _database_code_depnum_ccdc_archive 'CCDC 854568' #TrackingRef '- Yufit_Howard.cif' _audit_creation_date 2010-10-08 _audit_creation_method ; Olex2 1.1-beta (compiled 2010.10.06 svn.r1460, GUI svn.r3288) ; _chemical_name_common 'dichloromethane cyclobutanone co-crystal' _chemical_name_systematic ; dichloromethane cyclobutanone clathrate (1:2) ; _chemical_formula_moiety 'C4 H6 O, 0.5 x C1 H2 Cl2' _chemical_formula_sum 'C9 H14 Cl2 O2' _chemical_formula_weight 225.10 _chemical_melting_point 185-186 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system orthorhombic _space_group_IT_number 62 _space_group_name_H-M_alt 'P n m a' _space_group_name_Hall '-P 2ac 2n' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x+1/2, -y, z+1/2' 3 'x+1/2, -y+1/2, -z+1/2' 4 '-x, y+1/2, -z' 5 '-x, -y, -z' 6 'x-1/2, y, -z-1/2' 7 '-x-1/2, y-1/2, z-1/2' 8 'x, -y-1/2, z' _cell_length_a 10.3053(12) _cell_length_b 20.118(2) _cell_length_c 5.5119(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1142.7(2) _cell_formula_units_Z 4 _cell_measurement_reflns_used 1086 _cell_measurement_temperature 180.0(2) _cell_measurement_theta_max 28.94 _cell_measurement_theta_min 3.96 _exptl_absorpt_coefficient_mu 0.537 _exptl_absorpt_correction_T_max ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_type none _exptl_absorpt_process_details ? _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.308 _exptl_crystal_density_meas . _exptl_crystal_density_method 'not measured' _exptl_crystal_description cylinder _exptl_crystal_F_000 472 _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.30 _exptl_special_details ; The crystal to detector distance was 4.85 cm. ; _diffrn_reflns_av_R_equivalents 0.0677 _diffrn_reflns_av_unetI/netI 0.0426 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 28 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_l_max 5 _diffrn_reflns_limit_l_min -4 _diffrn_reflns_number 9197 _diffrn_reflns_theta_full 30.00 _diffrn_reflns_theta_max 30.00 _diffrn_reflns_theta_min 2.02 _diffrn_ambient_temperature 180.0(2) _diffrn_detector_area_resol_mean ? _diffrn_measured_fraction_theta_full 0.792 _diffrn_measured_fraction_theta_max 0.792 _diffrn_measurement_device_type 'Bruker SMART CCD 6000 area detector' _diffrn_measurement_method '/w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source_current 30.0 _diffrn_source_power 1.5 _diffrn_source_target MO _diffrn_source_voltage 50.0 _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 923 _reflns_number_total 1360 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement 'SAINT v6.45A (Bruker, 2003)' _computing_data_collection 'SMART v5.625 (Bruker, 2001)' _computing_data_reduction 'SAINT v6.45A (Bruker, 2003)' _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _refine_diff_density_max 0.167 _refine_diff_density_min -0.219 _refine_diff_density_rms 0.036 _refine_ls_extinction_coef 0.126(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL _refine_ls_goodness_of_fit_ref 1.072 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 93 _refine_ls_number_reflns 1360 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0555 _refine_ls_R_factor_gt 0.0325 _refine_ls_restrained_S_all 1.072 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details ; calc w=1/[\s^2^(Fo^2^)+(0.0300P)^2^+0.1000P] where P=(Fo^2^+2Fc^2^)/3 ; _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0730 _refine_ls_wR_factor_ref 0.0792 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _atom_sites_solution_hydrogens difmap _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.51729(6) 0.2500 -0.19167(13) 0.0613(3) Uani 1 2 d S . . Cl2 Cl 0.75403(6) 0.2500 0.09371(14) 0.0734(3) Uani 1 2 d S . . O1 O 0.53666(10) 0.39516(5) 0.36012(19) 0.0457(3) Uani 1 1 d . . . C1 C 0.61449(12) 0.40471(6) 0.5191(3) 0.0338(3) Uani 1 1 d . . . C1S C 0.5836(2) 0.2500 0.1010(4) 0.0479(6) Uani 1 2 d S . . C2 C 0.61138(13) 0.44373(8) 0.7521(3) 0.0402(4) Uani 1 1 d . . . C3 C 0.76037(14) 0.43508(9) 0.7660(3) 0.0468(4) Uani 1 1 d . . . C4 C 0.75626(14) 0.38665(8) 0.5509(3) 0.0418(4) Uani 1 1 d . . . H1 H 0.5573(15) 0.2901(8) 0.180(3) 0.058(5) Uiso 1 1 d . . . H2A H 0.5684(15) 0.4221(9) 0.870(3) 0.049(5) Uiso 1 1 d . . . H2B H 0.5811(13) 0.4891(9) 0.737(3) 0.045(4) Uiso 1 1 d . . . H3A H 0.7895(16) 0.4184(9) 0.907(3) 0.055(5) Uiso 1 1 d . . . H3B H 0.8096(17) 0.4802(10) 0.724(4) 0.071(5) Uiso 1 1 d . . . H4A H 0.7657(15) 0.3415(9) 0.596(3) 0.056(5) Uiso 1 1 d . . . H4B H 0.8105(16) 0.3951(9) 0.414(3) 0.056(5) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0592(4) 0.0651(4) 0.0597(5) 0.000 -0.0097(3) 0.000 Cl2 0.0515(4) 0.1011(6) 0.0674(6) 0.000 -0.0060(3) 0.000 O1 0.0443(6) 0.0498(6) 0.0432(8) -0.0058(5) -0.0102(5) 0.0048(4) C1 0.0335(7) 0.0314(7) 0.0366(10) 0.0041(6) 0.0005(6) 0.0007(5) C1S 0.0551(13) 0.0422(12) 0.0463(17) 0.000 0.0066(10) 0.000 C2 0.0366(7) 0.0441(9) 0.0401(11) -0.0025(7) 0.0004(6) 0.0025(6) C3 0.0389(7) 0.0581(11) 0.0433(13) -0.0040(8) -0.0096(6) 0.0024(7) C4 0.0356(7) 0.0462(9) 0.0436(12) 0.0006(7) 0.0002(6) 0.0061(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 C1S 1.752(3) . ? Cl2 C1S 1.756(2) . ? O1 O1 0.000(3) 1 ? O1 C1 1.2036(16) . ? C1 O1 1.2036(16) 1 ? C1 C2 1.505(2) . ? C1 C4 1.5156(18) . ? C1S H1 0.957(17) . ? C2 C3 1.5471(19) . ? C2 H2A 0.898(16) . ? C2 H2B 0.968(16) . ? C3 C4 1.535(2) . ? C3 H3A 0.899(17) . ? C3 H3B 1.07(2) . ? C4 H4A 0.947(18) . ? C4 H4B 0.955(18) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag Cl1 C1S Cl2 111.66(13) . . ? Cl1 C1S H1 108.1(10) . . ? Cl2 C1S H1 107.1(10) . . ? O1 O1 C1 0(10) 1 . ? O1 C1 O1 0.00(12) 1 . ? O1 C1 C2 133.66(12) 1 . ? O1 C1 C2 133.66(12) . . ? O1 C1 C4 133.49(14) . . ? O1 C1 C4 133.49(14) 1 . ? C1 C2 C3 87.86(11) . . ? C1 C2 H2A 112.0(11) . . ? C1 C2 H2B 115.1(10) . . ? C1 C4 C3 87.92(11) . . ? C1 C4 H4A 111.0(10) . . ? C1 C4 H4B 115.4(10) . . ? C2 C1 C4 92.70(11) . . ? C2 C3 H3A 114.6(11) . . ? C2 C3 H3B 111.5(9) . . ? C3 C2 H2A 113.5(10) . . ? C3 C2 H2B 115.5(9) . . ? C3 C4 H4A 113.7(10) . . ? C3 C4 H4B 118.8(11) . . ? C4 C3 C2 90.32(11) . . ? C4 C3 H3A 116.2(12) . . ? C4 C3 H3B 112.6(11) . . ? H2A C2 H2B 111.1(15) . . ? H3A C3 H3B 110.4(15) . . ? H4A C4 H4B 108.6(14) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C1S H1 O1 0.957(17) 2.344(17) 3.2866(15) 168.2(13) . #==END data_3_DCH _database_code_depnum_ccdc_archive 'CCDC 854569' #TrackingRef '- Yufit_Howard.cif' _audit_creation_method SHELXL-97 _chemical_formula_moiety 'C6 H10 O, C H2 Cl2' _chemical_formula_sum 'C7 H12 Cl2 O' _chemical_formula_weight 183.07 _chemical_melting_point '195 - 196' _chemical_name_common 'dichloromethane cyclohexanone co-crystal' _chemical_name_systematic ; dichloromethane cyclohexanone clathrate (1:1) ; loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_angle_alpha 103.760(10) _cell_angle_beta 103.150(10) _cell_angle_gamma 98.400(10) _cell_formula_units_Z 2 _cell_length_a 6.2893(6) _cell_length_b 7.8029(9) _cell_length_c 10.3006(13) _cell_measurement_reflns_used 827 _cell_measurement_temperature 180.0(2) _cell_measurement_theta_max 28.93 _cell_measurement_theta_min 2.75 _cell_volume 467.28(9) _exptl_absorpt_coefficient_mu 0.632 _exptl_absorpt_correction_T_max ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_type none _exptl_absorpt_process_details ? _exptl_crystal_F_000 192 _exptl_crystal_colour 'dull light colourless' _exptl_crystal_colour_lustre dull _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.301 _exptl_crystal_density_meas . _exptl_crystal_density_method 'not measured' _exptl_crystal_description cylinder _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.3 _exptl_special_details ? _diffrn_ambient_temperature 180.0(2) _diffrn_detector 'CCD area detector' _diffrn_detector_area_resol_mean 8.0 _diffrn_detector_type 'Bruker SMART CCD 6000 area detector' _diffrn_measured_fraction_theta_full 0.747 _diffrn_measured_fraction_theta_max 0.747 _diffrn_measurement_device 'three-circle diffractometer' _diffrn_measurement_device_type 'Bruker SMART CCD 6000 area detector' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_xray_symbol K-L~3~ _diffrn_reflns_av_R_equivalents 0.0150 _diffrn_reflns_av_sigmaI/netI 0.0214 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 4033 _diffrn_reflns_theta_full 29.99 _diffrn_reflns_theta_max 29.99 _diffrn_reflns_theta_min 2.12 _diffrn_source 'sealed X-ray tube' _diffrn_source_current 30.0 _diffrn_source_power 1.35 _diffrn_source_target Mo _diffrn_source_voltage 45.0 _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 1519 _reflns_number_total 2029 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement 'SAINT v6.45A (Bruker, 2003)' _computing_data_collection 'SMART v5.625 (Bruker, 2001)' _computing_data_reduction 'SAINT v6.45A (Bruker, 2003)' _computing_molecular_graphics ; OLEX2: a complete structure solution, refinement and analysis program. Dolomanov et al., J. Appl. Cryst. (2009). 42, 339-341 ; _computing_publication_material ; OLEX2: a complete structure solution, refinement and analysis program. Dolomanov et al., J. Appl. Cryst. (2009). 42, 339-341 ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)/Bruker' _refine_diff_density_max 0.319 _refine_diff_density_min -0.222 _refine_diff_density_rms 0.036 _refine_ls_R_factor_all 0.0453 _refine_ls_R_factor_gt 0.0339 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 139 _refine_ls_number_reflns 2029 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.048 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_wR_factor_gt 0.0912 _refine_ls_wR_factor_ref 0.0977 _refine_ls_weighting_details ; calc w=1/[\s^2^(Fo^2^)+(0.0500P)^2^+0.0500P] where P=(Fo^2^+2Fc^2^)/3 ; _refine_ls_weighting_scheme calc _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _atom_sites_solution_hydrogens difmap _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.1283(2) -0.16178(15) 0.55447(11) 0.0529(3) Uani 1 1 d . . . C1 C 0.1910(3) -0.02002(19) 0.64628(13) 0.0393(4) Uani 1 1 d . . . C2 C 0.4148(4) 0.0996(3) 0.67394(17) 0.0546(5) Uani 1 1 d . . . C3 C 0.5433(3) 0.1561(3) 0.82754(17) 0.0541(5) Uani 1 1 d . . . C4 C 0.4045(3) 0.2329(2) 0.91902(16) 0.0469(4) Uani 1 1 d . . . C5 C 0.1859(3) 0.1011(2) 0.89323(15) 0.0476(4) Uani 1 1 d . . . C6 C 0.0526(3) 0.0458(2) 0.74044(16) 0.0431(4) Uani 1 1 d . . . H2A H 0.375(4) 0.212(3) 0.650(2) 0.060(6) Uiso 1 1 d . . . H2B H 0.494(5) 0.041(3) 0.615(3) 0.088(8) Uiso 1 1 d . . . H3A H 0.684(4) 0.239(3) 0.841(2) 0.078(7) Uiso 1 1 d . . . H3B H 0.586(4) 0.054(3) 0.853(2) 0.065(6) Uiso 1 1 d . . . H4A H 0.366(3) 0.345(3) 0.900(2) 0.060(6) Uiso 1 1 d . . . H4B H 0.486(4) 0.259(3) 1.012(2) 0.061(6) Uiso 1 1 d . . . H5A H 0.229(3) -0.009(3) 0.9184(19) 0.057(5) Uiso 1 1 d . . . H5B H 0.098(4) 0.153(3) 0.953(2) 0.062(6) Uiso 1 1 d . . . H6A H 0.010(3) 0.151(3) 0.7176(19) 0.054(5) Uiso 1 1 d . . . H6B H -0.078(4) -0.042(3) 0.7227(19) 0.058(5) Uiso 1 1 d . . . Cl1 Cl 0.57747(9) 0.61087(6) 0.68816(5) 0.06150(19) Uani 1 1 d . . . Cl2 Cl 1.02434(10) 0.56155(7) 0.80018(6) 0.0748(2) Uani 1 1 d . . . C1S C 0.8111(3) 0.5350(2) 0.64803(18) 0.0485(4) Uani 1 1 d . . . H1SA H 0.764(3) 0.410(3) 0.5993(18) 0.052(5) Uiso 1 1 d . . . H1SB H 0.867(3) 0.606(3) 0.594(2) 0.054(5) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0699(10) 0.0442(6) 0.0386(5) 0.0007(4) 0.0107(5) 0.0182(6) C1 0.0487(11) 0.0399(7) 0.0292(6) 0.0101(5) 0.0064(6) 0.0151(7) C2 0.0508(13) 0.0725(12) 0.0384(8) 0.0107(8) 0.0181(7) 0.0056(10) C3 0.0422(12) 0.0681(12) 0.0441(8) 0.0070(8) 0.0091(7) 0.0056(9) C4 0.0474(11) 0.0474(8) 0.0349(7) 0.0006(6) 0.0042(6) 0.0058(8) C5 0.0535(13) 0.0516(9) 0.0359(7) 0.0054(6) 0.0188(7) 0.0069(8) C6 0.0393(11) 0.0387(7) 0.0443(8) 0.0019(6) 0.0094(6) 0.0059(7) Cl1 0.0544(4) 0.0644(3) 0.0601(3) 0.0014(2) 0.0163(2) 0.0209(2) Cl2 0.0644(4) 0.0560(3) 0.0840(4) 0.0104(2) -0.0113(3) 0.0165(3) C1S 0.0477(12) 0.0398(8) 0.0522(9) 0.0029(7) 0.0121(7) 0.0104(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.2160(17) . ? C1 C6 1.497(2) . ? C1 C2 1.497(2) . ? C2 C3 1.527(2) . ? C2 H2A 1.01(2) . ? C2 H2B 0.95(3) . ? C3 C4 1.506(3) . ? C3 H3A 0.98(2) . ? C3 H3B 0.95(2) . ? C4 C5 1.519(2) . ? C4 H4A 0.99(2) . ? C4 H4B 0.93(2) . ? C5 C6 1.529(2) . ? C5 H5A 1.01(2) . ? C5 H5B 0.98(2) . ? C6 H6A 0.96(2) . ? C6 H6B 0.94(2) . ? Cl1 C1S 1.759(2) . ? Cl2 C1S 1.7624(18) . ? C1S H1SA 0.955(19) . ? C1S H1SB 0.95(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 C6 122.67(15) . . ? O1 C1 C2 121.93(17) . . ? C6 C1 C2 115.39(14) . . ? C1 C2 C3 112.05(14) . . ? C1 C2 H2A 103.0(12) . . ? C3 C2 H2A 107.5(11) . . ? C1 C2 H2B 108.8(16) . . ? C3 C2 H2B 113.4(17) . . ? H2A C2 H2B 111.7(19) . . ? C4 C3 C2 111.75(17) . . ? C4 C3 H3A 112.9(15) . . ? C2 C3 H3A 109.0(14) . . ? C4 C3 H3B 108.8(14) . . ? C2 C3 H3B 109.3(13) . . ? H3A C3 H3B 105(2) . . ? C3 C4 C5 111.37(14) . . ? C3 C4 H4A 111.0(12) . . ? C5 C4 H4A 107.0(12) . . ? C3 C4 H4B 108.9(13) . . ? C5 C4 H4B 109.4(12) . . ? H4A C4 H4B 109.1(16) . . ? C4 C5 C6 111.39(13) . . ? C4 C5 H5A 105.8(12) . . ? C6 C5 H5A 108.9(11) . . ? C4 C5 H5B 110.3(12) . . ? C6 C5 H5B 111.2(13) . . ? H5A C5 H5B 109.2(16) . . ? C1 C6 C5 111.69(14) . . ? C1 C6 H6A 106.3(12) . . ? C5 C6 H6A 108.4(11) . . ? C1 C6 H6B 110.3(13) . . ? C5 C6 H6B 111.7(11) . . ? H6A C6 H6B 108.1(18) . . ? Cl1 C1S Cl2 111.08(10) . . ? Cl1 C1S H1SA 107.8(12) . . ? Cl2 C1S H1SA 108.5(11) . . ? Cl1 C1S H1SB 108.0(13) . . ? Cl2 C1S H1SB 108.6(12) . . ? H1SA C1S H1SB 112.8(16) . . ? #==END data_4_CMEK _database_code_depnum_ccdc_archive 'CCDC 854570' #TrackingRef '- Yufit_Howard.cif' _audit_creation_method SHELXL-97 _chemical_formula_moiety 'C4 H8 O, 2 CHCl3' _chemical_formula_sum 'C6 H10 Cl6 O' _chemical_formula_weight 310.84 _chemical_melting_point '175 - 179' _chemical_name_common 'chloroform methylethylketone co-crystal' _chemical_name_systematic ; trichloromethane butanone-2 clathrate (2:1) ; _chemical_absolute_configuration ad loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 n 1' _symmetry_space_group_name_Hall 'P -2yac' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y, z+1/2' _cell_angle_alpha 90.00 _cell_angle_beta 95.86(3) _cell_angle_gamma 90.00 _cell_formula_units_Z 2 _cell_length_a 6.054(2) _cell_length_b 6.965(3) _cell_length_c 16.346(6) _cell_measurement_reflns_used 480 _cell_measurement_temperature 165.0(2) _cell_measurement_theta_max 22.94 _cell_measurement_theta_min 2.50 _cell_volume 685.6(4) _exptl_absorpt_coefficient_mu 1.218 _exptl_absorpt_correction_T_max ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_type none _exptl_absorpt_process_details ? _exptl_crystal_F_000 312 _exptl_crystal_colour less _exptl_crystal_colour_lustre dull _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.506 _exptl_crystal_density_meas . _exptl_crystal_density_method 'not measured' _exptl_crystal_description cylinder _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _exptl_special_details ; The data collection nominally covered a full sphere of reciprocal space by a combination of 5 sets of \w scans each set at different \f and/or 2\q angles and each scan (10.00 s exposure) covering -0.300\ degrees in \w. The crystal to detector distance was 4.85 cm. ; _diffrn_ambient_temperature 165.0(2) _diffrn_detector 'CCD area detector' _diffrn_detector_area_resol_mean 5.6 _diffrn_detector_type 'Bruker SMART CCD 6000 area detector' _diffrn_measured_fraction_theta_full 0.875 _diffrn_measured_fraction_theta_max 0.875 _diffrn_measurement_device 'three-circle diffractometer' _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator Parallel,graphite _diffrn_radiation_probe x-ray _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type 'MO K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_xray_symbol K-L~3~ _diffrn_reflns_av_R_equivalents 0.0830 _diffrn_reflns_av_sigmaI/netI 0.0893 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_number 4192 _diffrn_reflns_theta_full 27.49 _diffrn_reflns_theta_max 27.49 _diffrn_reflns_theta_min 2.51 _diffrn_source 'sealed X-ray tube' _diffrn_source_current 40.0 _diffrn_source_power 2.0 _diffrn_source_target MO _diffrn_source_voltage 50.0 _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 1398 _reflns_number_total 2599 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement 'SAINT v6.45A (Bruker, 2003)' _computing_data_collection 'SMART v5.625 (Bruker, 2001)' _computing_data_reduction 'SAINT v6.45A (Bruker, 2003)' _computing_molecular_graphics ; OLEX2: a complete structure solution, refinement and analysis program. Dolomanov et al., J. Appl. Cryst. (2009). 42, 339-341 ; _computing_publication_material ; OLEX2: a complete structure solution, refinement and analysis program. Dolomanov et al., J. Appl. Cryst. (2009). 42, 339-341 ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)/Bruker' _refine_diff_density_max 0.349 _refine_diff_density_min -0.285 _refine_diff_density_rms 0.067 _refine_ls_R_factor_all 0.1068 _refine_ls_R_factor_gt 0.0497 _refine_ls_abs_structure_Flack -0.13(16) _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.957 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 121 _refine_ls_number_reflns 2599 _refine_ls_number_restraints 2 _refine_ls_restrained_S_all 0.957 _refine_ls_shift/su_max 0.115 _refine_ls_shift/su_mean 0.009 _refine_ls_structure_factor_coef Fsqd _refine_ls_wR_factor_gt 0.1044 _refine_ls_wR_factor_ref 0.1205 _refine_ls_weighting_details ; calc w=1/[\s^2^(Fo^2^)+(0.0400P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3 ; _refine_ls_weighting_scheme calc _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.0323(3) 0.7436(3) 0.34506(10) 0.0678(5) Uani 1 1 d . . . Cl2 Cl -0.0027(3) 0.6801(3) 0.17007(13) 0.0788(6) Uani 1 1 d . . . Cl3 Cl 0.4297(3) 0.7231(2) 0.26168(13) 0.0718(6) Uani 1 1 d . . . C1S C 0.1498(10) 0.7914(8) 0.2528(4) 0.0533(17) Uani 1 1 d . . . H1S H 0.1428 0.9331 0.2431 0.064 Uiso 1 1 calc R . . Cl4 Cl 0.4233(3) 1.0332(2) 0.05954(11) 0.0740(7) Uani 1 1 d . . . Cl5 Cl 0.4376(2) 1.4454(2) 0.04220(10) 0.0658(5) Uani 1 1 d . . . Cl6 Cl 0.0159(3) 1.2498(3) 0.03304(18) 0.1053(8) Uani 1 1 d . . . C2S C 0.2944(11) 1.2512(9) 0.0793(4) 0.0544(16) Uani 1 1 d . . . H2S H 0.281(9) 1.254(6) 0.140(3) 0.029(13) Uiso 1 1 d . . . O1 O 0.2962(17) 1.2166(14) 0.2834(7) 0.041(3) Uiso 0.50 1 d P A 1 C1 C 0.420(2) 1.2352(15) 0.3446(7) 0.035(2) Uiso 0.50 1 d P A 1 C2 C 0.323(3) 1.269(3) 0.4287(13) 0.052(5) Uiso 0.50 1 d P A 1 H2C H 0.2539 1.3969 0.4286 0.079 Uiso 0.50 1 calc PR A 1 H2B H 0.4423 1.2616 0.4737 0.079 Uiso 0.50 1 calc PR A 1 H2A H 0.2105 1.1714 0.4364 0.079 Uiso 0.50 1 calc PR A 1 C3 C 0.6683(19) 1.2540(15) 0.3444(7) 0.039(3) Uiso 0.50 1 d P A 1 H3A H 0.7426 1.1547 0.3808 0.047 Uiso 0.50 1 calc PR A 1 H3B H 0.7159 1.3813 0.3666 0.047 Uiso 0.50 1 calc PR A 1 C4 C 0.745(3) 1.231(2) 0.2531(10) 0.040(4) Uiso 0.50 1 d P A 1 H4A H 0.7143 1.0994 0.2335 0.060 Uiso 0.50 1 calc PR A 1 H4C H 0.9045 1.2565 0.2546 0.060 Uiso 0.50 1 calc PR A 1 H4B H 0.6628 1.3217 0.2158 0.060 Uiso 0.50 1 calc PR A 1 O1A O 0.3336(18) 1.2149(14) 0.2642(7) 0.040(3) Uiso 0.50 1 d P B 2 C1A C 0.514(2) 1.2309(15) 0.3063(7) 0.039(3) Uiso 0.50 1 d P B 2 C2A C 0.725(4) 1.241(3) 0.2736(12) 0.070(7) Uiso 0.50 1 d P B 2 H2AA H 0.7152 1.1777 0.2199 0.105 Uiso 0.50 1 calc PR B 2 H2AB H 0.8381 1.1774 0.3114 0.105 Uiso 0.50 1 calc PR B 2 H2AC H 0.7665 1.3763 0.2674 0.105 Uiso 0.50 1 calc PR B 2 C3A C 0.534(3) 1.240(2) 0.3942(10) 0.072(4) Uiso 0.50 1 d P B 2 H3AA H 0.5994 1.3653 0.4115 0.087 Uiso 0.50 1 calc PR B 2 H3AB H 0.6391 1.1388 0.4159 0.087 Uiso 0.50 1 calc PR B 2 C4A C 0.333(4) 1.217(3) 0.4310(15) 0.064(6) Uiso 0.50 1 d P B 2 H4AC H 0.2596 1.3415 0.4344 0.096 Uiso 0.50 1 calc PR B 2 H4AB H 0.3653 1.1633 0.4864 0.096 Uiso 0.50 1 calc PR B 2 H4AA H 0.2341 1.1288 0.3976 0.096 Uiso 0.50 1 calc PR B 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0703(12) 0.0791(12) 0.0542(11) 0.0014(9) 0.0075(8) -0.0043(9) Cl2 0.0777(13) 0.0995(14) 0.0578(11) -0.0106(11) 0.0002(9) -0.0248(11) Cl3 0.0495(10) 0.0538(9) 0.1123(16) 0.0149(10) 0.0091(10) 0.0075(8) C1S 0.048(4) 0.046(4) 0.064(4) 0.001(3) -0.003(3) -0.004(3) Cl4 0.0789(15) 0.0590(10) 0.0810(16) -0.0069(10) -0.0062(12) 0.0139(9) Cl5 0.0667(12) 0.0674(11) 0.0653(13) 0.0084(9) 0.0164(10) -0.0058(9) Cl6 0.0468(12) 0.0960(15) 0.166(2) -0.0329(16) -0.0238(13) -0.0008(10) C2S 0.053(4) 0.063(4) 0.047(4) 0.003(4) 0.002(3) -0.010(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 C1S 1.764(7) . ? Cl2 C1S 1.739(6) . ? Cl3 C1S 1.752(7) . ? C1S H1S 1.0000 . ? Cl4 C2S 1.752(7) . ? Cl5 C2S 1.749(7) . ? Cl6 C2S 1.776(7) . ? C2S H2S 1.00(5) . ? O1 C1 1.194(14) . ? C1 C2 1.57(2) . ? C1 C3 1.510(18) . ? C2 H2C 0.9800 . ? C2 H2B 0.9800 . ? C2 H2A 0.9800 . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C3 C4 1.616(19) . ? C4 H4A 0.9800 . ? C4 H4C 0.9800 . ? C4 H4B 0.9800 . ? O1A C1A 1.233(14) . ? C1A C2A 1.44(2) . ? C1A C3A 1.430(19) . ? C2A H2AA 0.9800 . ? C2A H2AB 0.9800 . ? C2A H2AC 0.9800 . ? C3A H3AA 0.9900 . ? C3A H3AB 0.9900 . ? C3A C4A 1.42(3) . ? C4A H4AC 0.9800 . ? C4A H4AB 0.9800 . ? C4A H4AA 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag Cl1 C1S H1S 107.9 . . ? Cl2 C1S Cl1 110.6(3) . . ? Cl2 C1S Cl3 112.1(4) . . ? Cl2 C1S H1S 107.9 . . ? Cl3 C1S Cl1 110.4(3) . . ? Cl3 C1S H1S 107.9 . . ? Cl4 C2S Cl6 109.7(4) . . ? Cl4 C2S H2S 106(3) . . ? Cl5 C2S Cl4 111.1(4) . . ? Cl5 C2S Cl6 109.8(4) . . ? Cl5 C2S H2S 115(3) . . ? Cl6 C2S H2S 105(3) . . ? O1 C1 C2 119.4(13) . . ? O1 C1 C3 123.2(12) . . ? C1 C3 H3A 109.2 . . ? C1 C3 H3B 109.2 . . ? C1 C3 C4 112.0(10) . . ? C3 C1 C2 116.9(11) . . ? H3A C3 H3B 107.9 . . ? C4 C3 H3A 109.2 . . ? C4 C3 H3B 109.2 . . ? O1A C1A C2A 124.5(13) . . ? O1A C1A C3A 123.1(13) . . ? C1A C2A H2AA 109.5 . . ? C1A C2A H2AB 109.5 . . ? C1A C2A H2AC 109.5 . . ? C1A C3A H3AA 108.4 . . ? C1A C3A H3AB 108.4 . . ? C1A C3A C4A 115.5(15) . . ? H2AA C2A H2AB 109.5 . . ? H2AA C2A H2AC 109.5 . . ? H2AB C2A H2AC 109.5 . . ? C3A C1A C2A 112.5(13) . . ? C3A C4A H4AC 109.5 . . ? C3A C4A H4AB 109.4 . . ? C3A C4A H4AA 109.5 . . ? H3AA C3A H3AB 107.4 . . ? C4A C3A H3AA 108.4 . . ? C4A C3A H3AB 108.4 . . ? H4AC C4A H4AB 109.5 . . ? H4AC C4A H4AA 109.5 . . ? H4AB C4A H4AA 109.5 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C1S H1S O1 1.00 2.25 3.117(11) 144.1 . C1S H1S O1A 1.00 2.29 3.152(12) 144.2 . C2S H2S O1 1.00(5) 2.35(6) 3.343(13) 170(4) . C2S H2S O1A 1.00(5) 2.04(6) 3.017(14) 164(4) . C4 H4C O1 0.98 2.39 3.324(19) 160.1 1_655 C4 H4C O1A 0.98 2.60 3.55(2) 162.9 1_655 #==END data_5_DB _database_code_depnum_ccdc_archive 'CCDC 854571' #TrackingRef '- Yufit_Howard.cif' _audit_creation_method SHELXL-97 _chemical_formula_moiety 'C4 H8 O, C H2 Cl2' _chemical_formula_sum 'C5 H10 Cl2 O' _chemical_formula_weight 157.03 _chemical_melting_point '168 - 170' _chemical_name_common 'dichloromethane methylethylketone co-crystal' _chemical_name_systematic ; dichloromethane butanone-2 clathrate (1:1) ; loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, y, z' 'x, -y-1/2, z-1/2' _cell_angle_alpha 90.00 _cell_angle_beta 102.77(2) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 8.5922(11) _cell_length_b 12.7617(18) _cell_length_c 7.6903(9) _cell_measurement_reflns_used 863 _cell_measurement_temperature 160.0(2) _cell_measurement_theta_max 27.02 _cell_measurement_theta_min 2.80 _cell_volume 822.39(18) _exptl_absorpt_coefficient_mu 0.706 _exptl_absorpt_correction_T_max ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_type none _exptl_absorpt_process_details ? _exptl_crystal_F_000 328 _exptl_crystal_colour less _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.268 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description cylinder _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _exptl_special_details ; The data collection nominally covered a full sphere of reciprocal space by a combination of 5 sets of \w scans each set at different \f and/or 2\q angles and each scan (10.00 s exposure) covering -0.300\ degrees in \w. The crystal to detector distance was 4.85 cm. ; _diffrn_ambient_temperature 160.0(2) _diffrn_detector 'CCD area detector' _diffrn_detector_area_resol_mean 5.6 _diffrn_detector_type 'Bruker SMART CCD 6000 area detector' _diffrn_measured_fraction_theta_full 0.877 _diffrn_measured_fraction_theta_max 0.877 _diffrn_measurement_device 'three-circle diffractometer' _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator Parallel,graphite _diffrn_radiation_probe x-ray _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type 'MO K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_xray_symbol K-L~3~ _diffrn_reflns_av_R_equivalents 0.0368 _diffrn_reflns_av_sigmaI/netI 0.0326 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_number 6089 _diffrn_reflns_theta_full 28.50 _diffrn_reflns_theta_max 28.50 _diffrn_reflns_theta_min 2.43 _diffrn_source 'sealed X-ray tube' _diffrn_source_current 30.0 _diffrn_source_power 1.5 _diffrn_source_target MO _diffrn_source_voltage 50.0 _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 1228 _reflns_number_total 1831 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement 'SAINT v6.45A (Bruker, 2003)' _computing_data_collection 'SMART v5.625 (Bruker, 2001)' _computing_data_reduction 'SAINT v6.45A (Bruker, 2003)' _computing_molecular_graphics ; OLEX2: a complete structure solution, refinement and analysis program. Dolomanov et al., J. Appl. Cryst. (2009). 42, 339-341 ; _computing_publication_material ; OLEX2: a complete structure solution, refinement and analysis program. Dolomanov et al., J. Appl. Cryst. (2009). 42, 339-341 ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)/Bruker' _refine_diff_density_max 0.276 _refine_diff_density_min -0.152 _refine_diff_density_rms 0.036 _refine_ls_R_factor_all 0.0531 _refine_ls_R_factor_gt 0.0303 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.004 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 113 _refine_ls_number_reflns 1831 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.004 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_wR_factor_gt 0.0648 _refine_ls_wR_factor_ref 0.0696 _refine_ls_weighting_details ; calc w=1/[\s^2^(Fo^2^)+(0.0300P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3 ; _refine_ls_weighting_scheme calc _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _atom_sites_solution_hydrogens difmap _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.58695(4) 0.66159(4) 0.94912(6) 0.05851(16) Uani 1 1 d . . . Cl2 Cl 0.93154(4) 0.67388(3) 1.01001(6) 0.05771(16) Uani 1 1 d . . . O1 O 0.75457(14) 0.55576(9) 0.50330(16) 0.0653(4) Uani 1 1 d . . . C1 C 0.8212(3) 0.43721(18) 0.2937(3) 0.0571(5) Uani 1 1 d . . . C1S C 0.74920(19) 0.70400(13) 0.8621(2) 0.0441(4) Uani 1 1 d . . . C2 C 0.76683(17) 0.46543(12) 0.4592(2) 0.0429(4) Uani 1 1 d . . . C3 C 0.7277(2) 0.37685(13) 0.5673(3) 0.0545(5) Uani 1 1 d . . . C4 C 0.6794(3) 0.40814(16) 0.7361(3) 0.0563(5) Uani 1 1 d . . . H1A H 0.752(3) 0.388(2) 0.225(4) 0.127(10) Uiso 1 1 d . . . H1B H 0.913(4) 0.409(2) 0.318(4) 0.147(12) Uiso 1 1 d . . . H1C H 0.829(3) 0.4923(19) 0.226(3) 0.098(8) Uiso 1 1 d . . . H1SA H 0.7446(19) 0.6643(13) 0.758(3) 0.056(5) Uiso 1 1 d . . . H1SB H 0.7427(18) 0.7765(14) 0.850(2) 0.051(5) Uiso 1 1 d . . . H3A H 0.649(3) 0.3392(16) 0.490(3) 0.086(7) Uiso 1 1 d . . . H3B H 0.826(2) 0.3321(15) 0.595(3) 0.089(7) Uiso 1 1 d . . . H4A H 0.657(2) 0.3488(16) 0.813(3) 0.094(7) Uiso 1 1 d . . . H4B H 0.590(3) 0.4525(17) 0.711(3) 0.096(8) Uiso 1 1 d . . . H4C H 0.762(2) 0.4464(15) 0.816(3) 0.073(6) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0409(2) 0.0695(3) 0.0665(4) -0.0136(2) 0.01474(19) 0.00185(19) Cl2 0.0418(2) 0.0699(3) 0.0626(3) 0.0059(2) 0.01402(19) -0.00218(19) O1 0.1038(11) 0.0314(6) 0.0584(10) -0.0007(5) 0.0133(8) -0.0006(6) C1 0.0623(12) 0.0586(12) 0.0547(14) -0.0010(10) 0.0222(10) -0.0068(10) C1S 0.0581(10) 0.0382(9) 0.0367(12) 0.0004(7) 0.0118(7) 0.0032(7) C2 0.0382(7) 0.0419(8) 0.0446(11) 0.0005(7) 0.0008(6) -0.0022(6) C3 0.0695(12) 0.0379(9) 0.0607(14) -0.0014(8) 0.0244(10) -0.0035(8) C4 0.0688(12) 0.0518(11) 0.0535(14) 0.0028(9) 0.0250(10) 0.0047(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 C1S 1.7595(17) . ? Cl2 C1S 1.7629(18) . ? O1 C2 1.2127(18) . ? C1 C2 1.494(3) . ? C1 H1A 0.94(3) . ? C1 H1B 0.85(3) . ? C1 H1C 0.89(2) . ? C1S H1SA 0.940(18) . ? C1S H1SB 0.931(17) . ? C2 C3 1.485(2) . ? C3 C4 1.502(3) . ? C3 H3A 0.93(2) . ? C3 H3B 1.00(2) . ? C4 H4A 1.00(2) . ? C4 H4B 0.94(2) . ? C4 H4C 0.96(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag Cl1 C1S Cl2 110.71(10) . . ? Cl1 C1S H1SA 105.6(11) . . ? Cl1 C1S H1SB 108.0(10) . . ? Cl2 C1S H1SA 107.2(10) . . ? Cl2 C1S H1SB 107.8(10) . . ? O1 C2 C1 122.01(16) . . ? O1 C2 C3 121.54(17) . . ? C2 C1 H1A 111.3(17) . . ? C2 C1 H1B 111(2) . . ? C2 C1 H1C 112.8(15) . . ? C2 C3 C4 114.91(16) . . ? C2 C3 H3A 105.0(14) . . ? C2 C3 H3B 105.7(12) . . ? C3 C2 C1 116.44(16) . . ? C3 C4 H4A 115.6(13) . . ? C3 C4 H4B 110.8(14) . . ? C3 C4 H4C 112.4(12) . . ? C4 C3 H3A 113.0(14) . . ? C4 C3 H3B 110.3(12) . . ? H1A C1 H1B 107(2) . . ? H1A C1 H1C 108(2) . . ? H1B C1 H1C 106(2) . . ? H1SA C1S H1SB 117.4(15) . . ? H3A C3 H3B 107.3(18) . . ? H4A C4 H4B 108.7(17) . . ? H4A C4 H4C 102.5(18) . . ? H4B C4 H4C 106.2(18) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C2 C3 C4 -2.4(3) . . . . ? C1 C2 C3 C4 177.84(18) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C1S H1SA O1 0.940(18) 2.417(19) 3.355(2) 175.1(14) . C1S H1SB O1 0.931(17) 2.435(17) 3.249(2) 146.2(14) 4_576 #==END data_6_cfac _database_code_depnum_ccdc_archive 'CCDC 854572' #TrackingRef '- Yufit_Howard.cif' _audit_creation_date 2010-11-03 _audit_creation_method ; Olex2 1.1-beta (compiled 2010.10.26 svn.r1482, GUI svn.r3310) ; _chemical_name_common 'Chloroform aceton co-crystal' _chemical_name_systematic ; trichloromethane propanone-2 clathrate (1:1) ; _chemical_formula_moiety 'C H Cl3, C3 H6 O' _chemical_formula_sum 'C4 H7 Cl3 O' _chemical_formula_weight 177.45 _chemical_melting_point '162 - 164.5' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 1 21/n 1' _space_group_name_Hall '-P 2yn' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x+1/2, y+1/2, -z+1/2' 3 '-x, -y, -z' 4 'x-1/2, -y-1/2, z-1/2' _cell_length_a 5.8895(4) _cell_length_b 13.6031(10) _cell_length_c 10.0396(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.99(2) _cell_angle_gamma 90.00 _cell_volume 804.21(10) _cell_formula_units_Z 4 _cell_measurement_reflns_used 1759 _cell_measurement_temperature 150.0(2) _cell_measurement_theta_max 30.45 _cell_measurement_theta_min 2.50 _exptl_absorpt_coefficient_mu 1.053 _exptl_absorpt_correction_T_max ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_type none _exptl_absorpt_process_details ? _exptl_crystal_colour less _exptl_crystal_colour_lustre dull _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary white _exptl_crystal_density_diffrn 1.466 _exptl_crystal_density_meas 0 _exptl_crystal_density_method 'not measured' _exptl_crystal_description cylinder _exptl_crystal_F_000 360 _exptl_crystal_preparation ? _exptl_crystal_recrystallization_method 'grown in situ at 160K' _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.30 _exptl_special_details ; The data collection nominally covered a full sphere of reciprocal space by a combination of 5 sets of \w scans each set at different \f and/or 2\q angles and each scan (10.00 s exposure) covering -0.300\ degrees in \w. The crystal to detector distance was 4.85 cm. ; _diffrn_reflns_av_R_equivalents 0.0381 _diffrn_reflns_av_unetI/netI 0.0392 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 7047 _diffrn_reflns_theta_full 29.99 _diffrn_reflns_theta_max 29.99 _diffrn_reflns_theta_min 2.52 _diffrn_ambient_temperature 150.0(2) _diffrn_detector 'CCD area detector' _diffrn_detector_area_resol_mean 5.6 _diffrn_detector_type 'Bruker SMART CCD 6000 area detector' _diffrn_measured_fraction_theta_full 0.968 _diffrn_measured_fraction_theta_max 0.968 _diffrn_measurement_device 'three-circle diffractometer' _diffrn_measurement_device_type 'Bruker SMART CCD 6000 area detector' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_xray_symbol K-L~3~ _diffrn_source 'sealed X-ray tube' _diffrn_source_current 30.0 _diffrn_source_power 1.5 _diffrn_source_target Mo _diffrn_source_voltage 50.0 _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 1883 _reflns_number_total 2268 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement 'SAINT v6.45A (Bruker, 2003)' _computing_data_collection 'SMART v5.625 (Bruker, 2001)' _computing_data_reduction 'SAINT v6.45A (Bruker, 2003)' _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'A short history of SHELX (Sheldrick, 2007)/Bruker' _refine_diff_density_max 0.376 _refine_diff_density_min -0.233 _refine_diff_density_rms 0.062 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.061 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 101 _refine_ls_number_reflns 2268 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0359 _refine_ls_R_factor_gt 0.0289 _refine_ls_restrained_S_all 1.061 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details ; calc w=1/[\s^2^(Fo^2^)+(0.0400P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' ; _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0736 _refine_ls_wR_factor_ref 0.0772 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _atom_sites_solution_hydrogens difmap _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.40558(6) 0.72482(2) 0.30271(3) 0.03984(11) Uani 1 1 d . . . Cl2 Cl 0.82565(6) 0.73141(3) 0.45562(3) 0.04315(11) Uani 1 1 d . . . Cl3 Cl 0.39674(6) 0.74139(3) 0.58997(3) 0.04328(11) Uani 1 1 d . . . O1 O 0.30909(19) 0.48467(8) 0.37084(10) 0.0518(3) Uani 1 1 d . . . C1 C 0.1852(2) 0.48718(8) 0.27288(12) 0.0358(3) Uani 1 1 d . . . C1S C 0.54117(19) 0.69129(9) 0.45389(10) 0.0292(2) Uani 1 1 d . . . C2 C -0.0670(3) 0.48957(12) 0.28333(17) 0.0486(3) Uani 1 1 d . . . C3 C 0.2818(3) 0.48895(13) 0.13559(16) 0.0502(4) Uani 1 1 d . . . H1S H 0.538(2) 0.6256(11) 0.4624(12) 0.030(3) Uiso 1 1 d . . . H2C H -0.116(3) 0.5476(15) 0.237(2) 0.082(6) Uiso 1 1 d . . . H2B H -0.120(3) 0.4912(13) 0.375(2) 0.072(6) Uiso 1 1 d . . . H2A H -0.120(3) 0.4379(14) 0.235(2) 0.080(6) Uiso 1 1 d . . . H3C H 0.224(4) 0.5512(16) 0.091(2) 0.093(7) Uiso 1 1 d . . . H3B H 0.424(4) 0.4848(17) 0.133(2) 0.090(8) Uiso 1 1 d . . . H3A H 0.214(3) 0.4376(14) 0.088(2) 0.082(6) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0496(2) 0.03940(17) 0.03010(16) 0.00539(11) -0.01253(13) -0.00431(14) Cl2 0.02914(19) 0.0593(2) 0.04108(19) -0.00416(13) 0.00123(13) -0.00873(14) Cl3 0.0385(2) 0.0585(2) 0.03304(17) -0.00638(13) 0.00654(13) -0.00011(14) O1 0.0640(7) 0.0471(5) 0.0435(5) 0.0112(4) -0.0186(5) -0.0070(5) C1 0.0458(7) 0.0247(5) 0.0368(6) 0.0027(4) -0.0063(5) -0.0021(5) C1S 0.0305(6) 0.0329(6) 0.0242(5) 0.0003(4) -0.0022(4) -0.0027(5) C2 0.0470(8) 0.0449(8) 0.0539(8) -0.0029(7) 0.0004(6) 0.0048(7) C3 0.0553(10) 0.0534(9) 0.0420(7) -0.0027(6) 0.0015(6) -0.0058(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 C1S 1.7629(11) . ? Cl2 C1S 1.7619(12) . ? Cl3 C1S 1.7591(12) . ? O1 C1 1.2148(15) . ? C1 C2 1.491(2) . ? C1 C3 1.501(2) . ? C1S H1S 0.898(15) . ? C2 H2C 0.96(2) . ? C2 H2B 0.98(2) . ? C2 H2A 0.91(2) . ? C3 H3C 1.01(2) . ? C3 H3B 0.84(2) . ? C3 H3A 0.93(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag Cl1 C1S H1S 109.3(8) . . ? Cl2 C1S Cl1 110.18(6) . . ? Cl2 C1S H1S 109.0(8) . . ? Cl3 C1S Cl1 110.52(7) . . ? Cl3 C1S Cl2 110.17(6) . . ? Cl3 C1S H1S 107.6(8) . . ? O1 C1 C2 121.92(14) . . ? O1 C1 C3 120.80(15) . . ? C1 C2 H2C 105.9(12) . . ? C1 C2 H2B 113.8(12) . . ? C1 C2 H2A 106.3(13) . . ? C1 C3 H3C 106.6(12) . . ? C1 C3 H3B 114.7(15) . . ? C1 C3 H3A 107.1(12) . . ? C2 C1 C3 117.28(13) . . ? H2C C2 H2B 109.8(16) . . ? H2C C2 H2A 106.2(17) . . ? H2B C2 H2A 114.2(17) . . ? H3C C3 H3B 112(2) . . ? H3C C3 H3A 105.2(16) . . ? H3B C3 H3A 111(2) . . ? #==END data_7_dcmac _database_code_depnum_ccdc_archive 'CCDC 854573' #TrackingRef '- Yufit_Howard.cif' _audit_creation_date 2010-11-23 _audit_creation_method ; Olex2 1.1-beta (compiled 2010.10.26 svn.r1482, GUI svn.r3310) ; _chemical_name_common 'dichloromethane acetone co-crystal' _chemical_name_systematic ; dichloromethane propanone-2 clathrate (1:1) ; _chemical_formula_moiety 'C4 H6 O, C H2 Cl2' _chemical_formula_sum 'C4 H8 Cl2 O' _chemical_formula_weight 143.00 _chemical_melting_point '216 - 217' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system monoclinic _space_group_IT_number 15 _space_group_name_H-M_alt 'C 1 2/c 1' _space_group_name_Hall '-C 2yc' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, y, -z+1/2' 3 'x+1/2, y+1/2, z' 4 '-x+1/2, y+1/2, -z+1/2' 5 '-x, -y, -z' 6 'x, -y, z-1/2' 7 '-x+1/2, -y+1/2, -z' 8 'x+1/2, -y+1/2, z-1/2' _cell_length_a 14.5833(12) _cell_length_b 8.2213(7) _cell_length_c 13.9240(10) _cell_angle_alpha 90.00 _cell_angle_beta 117.210(10) _cell_angle_gamma 90.00 _cell_volume 1484.7(2) _cell_formula_units_Z 8 _cell_measurement_reflns_used 1129 _cell_measurement_temperature 200.0(2) _cell_measurement_theta_max 28.80 _cell_measurement_theta_min 2.93 _exptl_absorpt_coefficient_mu 0.776 _exptl_absorpt_correction_T_max ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_type none _exptl_absorpt_process_details ? _exptl_crystal_colour ? _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.280 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description ? _exptl_crystal_F_000 592 _exptl_crystal_recrystallization_method 'Cristallized in situ in 0.3mm capillary at 172K' _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.3 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0242 _diffrn_reflns_av_unetI/netI 0.0181 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_number 6403 _diffrn_reflns_theta_full 29.99 _diffrn_reflns_theta_max 29.99 _diffrn_reflns_theta_min 2.93 _diffrn_ambient_temperature 200.0(2) _diffrn_detector 'CCD area detector' _diffrn_detector_area_resol_mean 5.6 _diffrn_detector_type 'Bruker SMART CCD 6000 area detector' _diffrn_measured_fraction_theta_full 0.797 _diffrn_measured_fraction_theta_max 0.797 _diffrn_measurement_device 'three-circle diffractometer' _diffrn_measurement_device_type 'Bruker SMART CCD 6000 area detector' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_xray_symbol K-L~3~ _diffrn_source 'sealed X-ray tube' _diffrn_source_current 25.0 _diffrn_source_power 1.25 _diffrn_source_target Mo _diffrn_source_voltage 50.0 _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 1266 _reflns_number_total 1733 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement 'SAINT v6.45A (Bruker, 2003)' _computing_data_collection 'SMART v5.625 (Bruker, 2001)' _computing_data_reduction 'SAINT v6.45A (Bruker, 2003)' _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'A short history of SHELX (Sheldrick, 2007)/Bruker' _refine_diff_density_max 0.616 _refine_diff_density_min -0.360 _refine_diff_density_rms 0.050 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 96 _refine_ls_number_reflns 1733 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0550 _refine_ls_R_factor_gt 0.0418 _refine_ls_restrained_S_all 1.047 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details ; calc w=1/[\s^2^(Fo^2^)+(0.0800P)^2^+0.4500P] where P=(Fo^2^+2Fc^2^)/3' ; _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1275 _refine_ls_wR_factor_ref 0.1394 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _atom_sites_solution_hydrogens difmap _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.33227(6) 0.52018(7) 0.18633(7) 0.0736(3) Uani 1 1 d . . . Cl2 Cl 0.33722(6) 0.48809(7) 0.39659(6) 0.0759(3) Uani 1 1 d . . . C1S C 0.29968(14) 0.3968(2) 0.26994(16) 0.0485(5) Uani 1 1 d . . . H1SA H 0.2298(15) 0.390(3) 0.2363(16) 0.050(5) Uiso 1 1 d . . . H1SB H 0.3343(14) 0.302(3) 0.2824(14) 0.051(5) Uiso 1 1 d . . . O1 O 0.42848(10) 0.03821(17) 0.33243(13) 0.0597(4) Uani 1 1 d . . . C1 C 0.52066(14) 0.02107(19) 0.38338(16) 0.0411(4) Uani 1 1 d . . . C2 C 0.59008(19) 0.1645(3) 0.4255(3) 0.0642(6) Uani 1 1 d . . . H2A H 0.555(2) 0.270(3) 0.403(2) 0.079(7) Uiso 1 1 d . . . H2B H 0.636(2) 0.163(4) 0.398(3) 0.107(11) Uiso 1 1 d . . . H2C H 0.621(3) 0.171(4) 0.496(3) 0.109(12) Uiso 1 1 d . . . C3 C 0.56968(19) -0.1425(2) 0.4065(2) 0.0593(6) Uani 1 1 d . . . H3A H 0.522(2) -0.219(4) 0.378(2) 0.089(8) Uiso 1 1 d . . . H3B H 0.611(2) -0.153(3) 0.375(2) 0.078(8) Uiso 1 1 d . . . H3C H 0.607(2) -0.161(4) 0.480(3) 0.100(10) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0919(5) 0.0542(3) 0.0943(6) 0.0035(3) 0.0595(4) -0.0020(2) Cl2 0.0923(5) 0.0633(4) 0.0579(5) -0.0047(2) 0.0220(3) 0.0045(3) C1S 0.0459(9) 0.0334(7) 0.0612(12) -0.0004(7) 0.0203(8) 0.0015(6) O1 0.0475(7) 0.0482(7) 0.0774(11) -0.0035(6) 0.0235(7) 0.0007(5) C1 0.0507(9) 0.0401(8) 0.0383(11) -0.0017(6) 0.0253(7) -0.0012(6) C2 0.0610(12) 0.0481(10) 0.0765(18) -0.0069(10) 0.0255(11) -0.0115(9) C3 0.0655(12) 0.0432(9) 0.0701(17) 0.0035(9) 0.0318(12) 0.0082(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 C1S 1.765(2) . ? Cl2 C1S 1.758(2) . ? C1S H1SA 0.908(19) . ? C1S H1SB 0.90(2) . ? O1 C1 1.207(2) . ? C1 C2 1.489(3) . ? C1 C3 1.488(2) . ? C2 H2A 0.98(3) . ? C2 H2B 0.91(3) . ? C2 H2C 0.88(4) . ? C3 H3A 0.89(3) . ? C3 H3B 0.90(3) . ? C3 H3C 0.92(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag Cl1 C1S H1SA 105.7(13) . . ? Cl1 C1S H1SB 109.2(12) . . ? Cl2 C1S Cl1 111.22(10) . . ? Cl2 C1S H1SA 107.7(13) . . ? Cl2 C1S H1SB 106.6(12) . . ? H1SA C1S H1SB 116.6(18) . . ? O1 C1 C2 120.85(17) . . ? O1 C1 C3 121.89(17) . . ? C1 C2 H2A 114.6(15) . . ? C1 C2 H2B 109(2) . . ? C1 C2 H2C 113(2) . . ? C1 C3 H3A 110.0(18) . . ? C1 C3 H3B 110.4(18) . . ? C1 C3 H3C 112(2) . . ? H2A C2 H2B 105(3) . . ? H2A C2 H2C 103(3) . . ? H2B C2 H2C 112(3) . . ? C3 C1 C2 117.26(19) . . ? H3A C3 H3B 106(2) . . ? H3A C3 H3C 109(3) . . ? H3B C3 H3C 110(3) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C1S H1SA O1 0.908(19) 2.39(2) 3.181(2) 146.0(17) 4 C1S H1SB O1 0.90(2) 2.49(2) 3.388(2) 174.8(16) . #==END data_8_CD _database_code_depnum_ccdc_archive 'CCDC 854574' #TrackingRef '- Yufit_Howard.cif' _audit_creation_method SHELXL-97 _chemical_formula_moiety 'C H Cl3, 0.5 C4 H8 O2' _chemical_formula_sum 'C3 H5 Cl3 O' _chemical_formula_weight 163.42 _chemical_melting_point '205 - 206' _chemical_name_common 'chloroform dioxane co-crystal' _chemical_name_systematic ; trichloromethane 1,4-dioxane (2:1) ; loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_angle_alpha 90.00 _cell_angle_beta 100.93(2) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 5.9481(5) _cell_length_b 9.3502(8) _cell_length_c 12.1479(11) _cell_measurement_reflns_used 1549 _cell_measurement_temperature 200.0(2) _cell_measurement_theta_max 31.15 _cell_measurement_theta_min 2.18 _cell_volume 663.36(10) _exptl_absorpt_coefficient_mu 1.269 _exptl_absorpt_correction_T_max ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_type none _exptl_absorpt_process_details ? _exptl_crystal_F_000 328 _exptl_crystal_colour colourless _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.636 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description cylinder _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.3 _exptl_special_details ? _diffrn_ambient_temperature 200.0(2) _diffrn_detector 'CCD area detector' _diffrn_detector_area_resol_mean 5.6 _diffrn_detector_type 'Bruker SMART CCD 6000 area detector' _diffrn_measured_fraction_theta_full 0.776 _diffrn_measured_fraction_theta_max 0.776 _diffrn_measurement_device 'three-circle diffractometer' _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type 'MO K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_xray_symbol K-L~3~ _diffrn_reflns_av_R_equivalents 0.0379 _diffrn_reflns_av_sigmaI/netI 0.0234 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 5682 _diffrn_reflns_theta_full 30.00 _diffrn_reflns_theta_max 30.00 _diffrn_reflns_theta_min 2.77 _diffrn_source 'sealed X-ray tube' _diffrn_source_current 30.0 _diffrn_source_power 1.5 _diffrn_source_target Mo _diffrn_source_voltage 50.0 _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 1287 _reflns_number_total 1507 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement 'SAINT v6.45A (Bruker, 2003)' _computing_data_collection 'Bruker SMART' _computing_data_reduction 'SAINT v6.45A (Bruker, 2003)' _computing_molecular_graphics ; OLEX2: a complete structure solution, refinement and analysis program. Dolomanov et al., J. Appl. Cryst. (2009). 42, 339-341 ; _computing_publication_material ; OLEX2: a complete structure solution, refinement and analysis program. Dolomanov et al., J. Appl. Cryst. (2009). 42, 339-341 ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)/Bruker' _refine_diff_density_max 0.425 _refine_diff_density_min -0.398 _refine_diff_density_rms 0.054 _refine_ls_R_factor_all 0.0422 _refine_ls_R_factor_gt 0.0364 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.066 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 84 _refine_ls_number_reflns 1507 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.066 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_wR_factor_gt 0.0976 _refine_ls_wR_factor_ref 0.1043 _refine_ls_weighting_details ; calc w=1/[\s^2^(Fo^2^)+(0.0500P)^2^+0.3000P] where P=(Fo^2^+2Fc^2^)/3 ; _refine_ls_weighting_scheme calc _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _atom_sites_solution_hydrogens difmap _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.40741(12) 0.47821(6) 0.14712(5) 0.0535(2) Uani 1 1 d . . . Cl2 Cl 0.00124(13) 0.63018(7) 0.17988(6) 0.0634(2) Uani 1 1 d . . . Cl3 Cl -0.01706(13) 0.32588(7) 0.14001(6) 0.0672(2) Uani 1 1 d . . . O1 O 0.1877(3) 0.43141(14) 0.46605(11) 0.0412(4) Uani 1 1 d . . . C1S C 0.1547(4) 0.46877(19) 0.20090(15) 0.0391(5) Uani 1 1 d . . . C1 C -0.0138(4) 0.3546(2) 0.4782(2) 0.0469(6) Uani 1 1 d . . . C2 C 0.2192(4) 0.5494(2) 0.54219(18) 0.0458(5) Uani 1 1 d . . . H1S H 0.198(5) 0.451(2) 0.2789(19) 0.046(6) Uiso 1 1 d . . . H1A H -0.029(5) 0.283(3) 0.426(2) 0.062(7) Uiso 1 1 d . . . H1B H 0.016(5) 0.317(3) 0.554(2) 0.070(8) Uiso 1 1 d . . . H2A H 0.354(5) 0.596(3) 0.529(2) 0.055(7) Uiso 1 1 d . . . H2B H 0.243(5) 0.512(3) 0.622(2) 0.054(7) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0446(5) 0.0523(3) 0.0682(4) -0.0016(2) 0.0224(3) -0.0026(2) Cl2 0.0604(6) 0.0531(3) 0.0762(4) 0.0027(3) 0.0122(3) 0.0182(3) Cl3 0.0496(6) 0.0576(3) 0.0928(5) -0.0107(3) 0.0092(3) -0.0150(3) O1 0.0369(11) 0.0408(7) 0.0483(7) -0.0044(5) 0.0143(6) 0.0017(6) C1S 0.0361(15) 0.0430(9) 0.0381(8) 0.0021(7) 0.0064(7) 0.0001(7) C1 0.0497(18) 0.0333(8) 0.0613(12) -0.0065(8) 0.0198(10) -0.0051(8) C2 0.0386(18) 0.0519(11) 0.0470(10) -0.0102(8) 0.0080(9) -0.0081(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 C1S 1.751(2) . ? Cl2 C1S 1.757(2) . ? Cl3 C1S 1.758(2) . ? O1 C1 1.429(3) . ? O1 C2 1.429(2) . ? C1S H1S 0.95(2) . ? C1 C2 1.498(3) 3_566 ? C1 H1A 0.92(3) . ? C1 H1B 0.97(3) . ? C2 C1 1.498(3) 3_566 ? C2 H2A 0.96(3) . ? C2 H2B 1.01(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 C2 109.31(15) . . ? Cl1 C1S Cl2 111.19(10) . . ? Cl1 C1S Cl3 110.66(11) . . ? Cl2 C1S Cl3 110.32(13) . . ? Cl1 C1S H1S 107.0(16) . . ? Cl2 C1S H1S 109.4(15) . . ? Cl3 C1S H1S 108.2(15) . . ? O1 C1 C2 110.81(16) . 3_566 ? O1 C1 H1A 105.7(17) . . ? C2 C1 H1A 110.7(18) 3_566 . ? O1 C1 H1B 106.1(18) . . ? C2 C1 H1B 111.8(18) 3_566 . ? H1A C1 H1B 111(2) . . ? O1 C2 C1 110.65(18) . 3_566 ? O1 C2 H2A 104.8(15) . . ? C1 C2 H2A 112.5(17) 3_566 . ? O1 C2 H2B 109.0(14) . . ? C1 C2 H2B 109.2(16) 3_566 . ? H2A C2 H2B 111(2) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C1S H1S O1 0.95(2) 2.29(2) 3.209(2) 162(2) . #==END data_9_dd1 _database_code_depnum_ccdc_archive 'CCDC 854575' #TrackingRef '- Yufit_Howard.cif' _audit_creation_method ; manual editing of the CIF file created by SHELXTL Ver. 6.14 and processed with modiCIfer-09152005. ; _chemical_name_systematic ; dichloromethane 1,4-dioxane clathrate (2:1) ; _chemical_name_common 'dichloromethane dioxane co-crystal' _chemical_melting_point 205-206 _chemical_formula_moiety 'C4 H8 O2, 2 C H2 Cl2' _chemical_formula_sum 'C6 H12 Cl4 O2' _chemical_formula_weight 257.96 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P b c a ' _symmetry_space_group_name_Hall '-P 2ac 2ab ' _symmetry_int_tables_number 61 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 7.8287(13) _cell_length_b 10.025(2) _cell_length_c 14.764(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1158.8(4) _cell_formula_units_Z 4 _cell_measurement_temperature 195.0(2) _cell_measurement_reflns_used 1108 _cell_measurement_theta_min 2.76 _cell_measurement_theta_max 25.84 _exptl_crystal_description cylinder _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.479 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 528 _exptl_absorpt_coefficient_mu 0.985 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS (Bruker-AXS, 2003) ; _exptl_absorpt_correction_T_min 0.6940 _exptl_absorpt_correction_T_max 0.7565 _exptl_special_details ; ? ; _diffrn_ambient_temperature 195.0(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type Mo-K\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART CCD 6000' _diffrn_measurement_method '0.30\% \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8652 _diffrn_reflns_av_R_equivalents 0.0316 _diffrn_reflns_av_sigmaI/netI 0.0212 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.76 _diffrn_reflns_theta_max 29.00 _reflns_number_total 1462 _reflns_number_gt 1074 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART Ver. 5.630 (Bruker-AXS, 2003)' _computing_cell_refinement 'SAINT Ver. 6.45 (Bruker-AXS, 2003)' _computing_data_reduction 'SAINT Ver. 6.45' _computing_structure_solution 'SHELXTL Ver. 6.14 (Bruker-AXS, 2003)' _computing_structure_refinement 'SHELXTL Ver. 6.14' _computing_molecular_graphics 'SHELXTL Ver. 6.14' _computing_publication_material 'SHELXTL Ver. 6.14' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0300P)^2^+0.5000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0076(11) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1462 _refine_ls_number_parameters 80 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0512 _refine_ls_R_factor_gt 0.0326 _refine_ls_wR_factor_ref 0.0848 _refine_ls_wR_factor_gt 0.0753 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.032 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.04928(17) 0.48374(13) 0.09089(8) 0.0495(3) Uani 1 1 d . . . C1 C 0.0434(3) 0.37376(19) 0.02970(14) 0.0518(5) Uani 1 1 d . . . C2 C 0.0868(3) 0.60305(19) 0.04245(13) 0.0481(4) Uani 1 1 d . . . H11 H 0.010(3) 0.296(2) 0.0651(14) 0.063(6) Uiso 1 1 d . . . H12 H 0.153(3) 0.361(2) 0.0012(14) 0.062(6) Uiso 1 1 d . . . H21 H 0.197(3) 0.596(2) 0.0165(13) 0.050(5) Uiso 1 1 d . . . H22 H 0.088(3) 0.675(2) 0.0884(14) 0.066(6) Uiso 1 1 d . . . Cl1 Cl 0.01586(7) 0.47681(5) 0.37443(4) 0.06028(19) Uani 1 1 d . . . Cl2 Cl 0.18800(10) 0.26370(6) 0.27788(5) 0.0844(3) Uani 1 1 d . . . C1S C 0.1773(3) 0.43601(19) 0.29593(13) 0.0462(4) Uani 1 1 d . . . H1S H 0.149(3) 0.475(2) 0.2404(15) 0.053(5) Uiso 1 1 d . . . H2S H 0.281(3) 0.465(2) 0.3240(14) 0.062(6) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0590(8) 0.0540(7) 0.0354(6) 0.0037(5) -0.0022(6) 0.0023(6) C1 0.0631(13) 0.0411(9) 0.0512(10) 0.0060(8) 0.0052(9) 0.0083(9) C2 0.0501(12) 0.0468(9) 0.0474(10) -0.0057(8) 0.0064(9) -0.0058(8) Cl1 0.0573(4) 0.0632(3) 0.0604(3) -0.0054(2) 0.0075(2) 0.0054(2) Cl2 0.0963(5) 0.0491(3) 0.1078(5) 0.0019(3) 0.0394(4) 0.0094(3) C1S 0.0488(12) 0.0492(10) 0.0407(9) 0.0042(7) -0.0006(8) -0.0024(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C2 1.424(2) . yes O1 C1 1.426(2) . yes C1 C2 1.492(3) 5_565 yes C1 H11 0.97(2) . ? C1 H12 0.97(2) . ? C2 C1 1.492(3) 5_565 yes C2 H21 0.95(2) . ? C2 H22 0.99(2) . ? Cl1 C1S 1.763(2) . yes Cl2 C1S 1.750(2) . yes C1S H1S 0.93(2) . ? C1S H2S 0.96(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 O1 C1 109.75(14) . . yes O1 C1 C2 110.73(15) . 5_565 yes O1 C1 H11 106.6(12) . . ? C2 C1 H11 109.1(13) 5_565 . ? O1 C1 H12 110.4(13) . . ? C2 C1 H12 108.5(13) 5_565 . ? H11 C1 H12 111.5(18) . . ? O1 C2 C1 110.40(16) . 5_565 yes O1 C2 H21 109.1(12) . . ? C1 C2 H21 110.2(12) 5_565 . ? O1 C2 H22 105.5(12) . . ? C1 C2 H22 112.5(13) 5_565 . ? H21 C2 H22 108.9(18) . . ? Cl2 C1S Cl1 111.32(11) . . yes Cl2 C1S H1S 107.0(12) . . ? Cl1 C1S H1S 108.1(13) . . ? Cl2 C1S H2S 109.0(13) . . ? Cl1 C1S H2S 104.7(13) . . ? H1S C1S H2S 116.7(19) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C1S H1S O1 0.93(2) 2.34(2) 3.225(2) 156.8(17) . C1S H2S O1 0.96(2) 2.45(2) 3.391(3) 166.1(18) 6_656 _diffrn_measured_fraction_theta_max 0.948 _diffrn_reflns_theta_full 29.00 _diffrn_measured_fraction_theta_full 0.948 _refine_diff_density_max 0.247 _refine_diff_density_min -0.349 _refine_diff_density_rms 0.044 # File processed with modiCIFer Dec. 16,2005. I.A.Guzei, UW-Madison.